Despite being labeled as "country music" or "bluegrass",Like Red on a Rose had a mainstream sound to it, upsetting some fans, even making some of them believe that Jackson was abandoning his traditional past and aiming toward a more mainstream pop sound.
However, for his next album, he went back to his country roots. Jackson's newest studio album,Good Time, was released on March 4, 2008. The album's first single, "Small Town Southern Man", was released to radio on November 19.
"Country Boy", "Sissy's Song" and the final single from the album, "I Still Like Bologna", were also released as singles.
"Sissy's Song" is dedicated to a longtime friend of the Jackson family (Leslie "Sissy" Fitzgerald) who worked in their house everyday. Fitzgerald was killed in a motorcycle accident in mid-2007.
His sixteenth studio album,Freight Train, was released on March 30, 2010. The first single was "It's Just That Way", which debuted at #50 in January 2010. "Hard Hat and a Hammer" is the album's second single, released in May 2010.